How would you go about asking for a potential employer to pay for travel expenses and take it off from your first check?

Instead of looking at who does what .. why not look at the things that need to get done for a small techology team. Product: 6 people - 3 full stack engineers - 2 front end developers - 1 designer / product person Marketing & Community, 1 person - Full time hire, or CEO Support & Operations, 1 person - Part time hire, or CEO + Whole team I believe it's important for everyone on the team to help with support. Also, if you have a great product, then support shouldn't be that taxing. Q&A is usually needed when you have a bad development process (no unit testing or continuous integration deployments). Outsource everything else. - Bookeeping - HR stuff - Legal - Government program paperwork Hope that helps. P.S. I would put as many people on product as that's where you'll get the most bang for your buck.

I would be curious to know why you feel it is important to use personality testing. I have hired over 20 sales reps and I have never used any testing. I have conversations with my hires because that is going to tell me more about their personality any day than a test. Plus you might eliminate someone because of a test score that could be a great fit for your organization. I have a pretty strong process for hiring sales people and could share with you my steps and even the questions if you would like.

I'll divide your question into 2 questions, because I am not sure which one you're really asking :-) 1. Should I hire him despite the costs involved? You seem to already agree to this, based on what you wrote ("I am willing to set aside...assuming I see some ROI..."). 2. How to I justify his high salary to other employees? A few options: a. You don't tell them. b. The CEO's compensation can be structured in a way that his 'salary' isn't that high (and this is what the other employees will see - so no problems), and he gets a large bonus based on results (which could be measured within 6 months and then 12 months). This is also better for you seeing that you don't know how good is will be. Additionally, if he is so confident he can do the job, he shouldn't object to that structure. c. Make it clear to your employees, that if he manages to generate more income for the company, they too will benefit from it (end of the year bonus/increased salaries/holiday gifts?). d. the tough option: tell them that if you don't make some hard choices, there won't be a company for them to work at down the line (due to the yearly decrease in profits) It's your company (which you seem to have managed successfully), so I am sure that you know what would work best with your employees. I'm happy to help you construct the employment contract with the potential adviser. Good luck p.s.: let me know how things turned out. I'm curious :-)

Depending on what you need, you'll probably want to look at actual agencies. A single freelancer is unlikely to have the complete spectrum of skills you'll need, and unless you're looking to hire someone full-time, you'll probably have trouble retaining a single freelancer for a long period of time without conflicts. A mid-sized agency like the one I started (and later sold) specializes in designing and building sites. Their specialty is marketing and client acquisition, so they wouldn't be much help for the custom stuff later down the road — but that may not be an issue now. Another option may be to use a high-end development talent agency like http://www.10xmanagement.com/ — this company hires out very good developers, but you'll pay a premium. Like anything, you'll get what you pay for. Sometimes you'll get lucky on Elance, but you take on a lot of risk for the lower price. A mid-range agency has lower risk, but may lack full-stack capabilities. A high-range agency can solve all your problems, but you'll pay top dollar for it. I have a lot of experience screening and recruiting talent for projects in the mid-to-high range, so if you'd like to discuss strategies, let me know. Good luck!

I'd recommend RecruiterBox as long as you can focus on filing one position at a time. It let's you accept up to 200 applicants for 1 position for free. http://recruiterbox.com/recruitment-software-pricing-with-free-signup/ Also, There are quite a few others out there most of which offer free 30 day trials or free access to their platforms with feature limits on them vs the company's paid offerings. Based on the way you phrased the question, this app should do the trick! Side note - if you're making use off Google apps - just create a form for submissions. It's always free.